Method for synthesizing alpha-beta unsaturated acetyenic ketone compounds by carbonylation

Abstract

The invention discloses a method for synthesizing an alpha-beta unsaturated acetyenic ketone compound through carbonylation. The method is to take iodo arene, a terminal acetylene compound and carbon monoxide as reactants and activated carbon loaded palladium as a catalyst, to control the reaction temperature to be between 80 and 140 DEG C and the pressure of the carbon monoxide to be between 0.5 and 3.0 MPa in the presence of a catalyst accelerator and a reaction solvent, and to react for 1 to 4 hours to obtain products. The method can realize separation of the catalyst and the products after the reaction is over, and can reuse the catalyst and maintain the activity of the catalyst unchanged; and the selectivity is more than 99 percent, and the conversion rate is more than 90 percent. The method has good industrial application prospect.

Description

technical field [0001] The invention relates to a method for synthesizing α-β unsaturated acetylenic ketone compounds through Carbonylative Sonogashira Coupling (Carbonylative Sonogashira Coupling) of heterogeneous palladium-catalyzed iodobenzene compounds and terminal alkynes under mild conditions. Background technique [0002] α-β unsaturated alkyne ketones are extremely important organic intermediates, widely used in the synthesis of heterocyclic compounds, bioactive macromolecules (such as: vitamins, nucleosides, amino acids, etc.), natural products, drugs, etc. (reference : C. Chowdhury, N.G. Kundu, Tetrahedron 1999, 55, 7011 and references therein.). The traditional method (reference: L.Delaude, A.M.Masdeu, H.Alper, Synthesis 1994, 1149.) of synthesizing α-β unsaturated alkyne ketone mainly contains 1) the coupling reaction of the alkynyl compound of acid chloride and metal; 2) tin Or the coupling reaction of silicon alkynyl compounds with organic halides in the prese...

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Problems solved by technology

But these catalyst systems exist: 1) the toxicity of phosphine compound; 2) the inherent product of homogeneous catalyst and the defect that catalyst is difficult to separate

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